4-Chloro-6,7-dimethoxyquinazoline → HCID 11719743, compound

HRID 915822Notes

Reaction equation

HRID 915822 reaction equation
[N:1]1([S:7]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[CH2:18][NH:17][CH2:16][CH2:15]3)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][N:22]=1>CC(O)C>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][N:22]=[C:21]2[N:17]1[CH2:16][CH2:15][C:14]2[C:19](=[C:10]([S:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)(=[O:9])=[O:8])[CH:11]=[CH:12][CH:13]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 58959724HCID 58959724, compound

Product 1

HCID 11719743HCID 11719743, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8-(morpholine-4-sulfonyl)-1,2,3,4-tetrahydroisoquinoline (15.7 g, 55.6 mmol) and 4-chloro-6,7-dimethoxy-quinazoline (12.5 g, 55.6 mmol) were refluxed overnight in 2-propanol (400 mL). The solvent was removed under vacuum and the resultant solid was partitioned between aqueous ammonia and CH2Cl2. The mixture was extracted three times with CH2Cl2 and the combined extracts were dried and concentrated. Flash chromatography (0.1:3:97 NH4OH/MeOH/CH2Cl2) followed by recrystallization of the product fractions from EtOH provided, in two crops, 22.2 g (85%) of the title compound.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe resultant solid was partitioned between aqueous ammonia and CH2Cl2
  3. extractionThe mixture was extracted three times with CH2Cl2
  4. customthe combined extracts were dried
  5. concentrationconcentrated
  6. customFlash chromatography (0.1:3:97 NH4OH/MeOH/CH2Cl2) followed by recrystallization of the product fractions from EtOH

Sources & evidence

ORD record
ord-552d9580461444b8990e282566ea5662
Source dataset
uspto-grants-2007_09
Patent number
US07268142B2

Reaction notes

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